Triethylamine → N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide

HRID 38230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 38230
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]([OH:15])=O)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.Cl.[CH3:25][NH:26][O:27][CH3:28].CCN(CC)CC>C(Cl)Cl.CN(C=O)C>[CH3:28][O:27][N:26]([CH3:25])[C:13]([C:11]1[CH:10]=[N:9][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:17][CH:16]=2)[CH:12]=1)=[O:15]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 435653621-[(4-methoxyphenyl)methyl]-1H-pyrazole-4-carboxylic acid

Produkt 1

HCID 86642328N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamideAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

According to Scheme 3 Step 1: A solution of 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylic acid (34.4 mmol, 8.00 g), oxalyl chloride (68.9 mmol, 5.92 mL) and a drop of DMF in DCM (80 mL) was stirred for 1 hour at room temperature. After evaporation, the crude product was dissolved in DCM (30 mL) and was added at 0° C. to a solution of N,O-dimethylhydroxylamine hydrochloride (103 mmol, 6.31 g) in DCM (100 mL) followed by Et3N (138 mmol, 19.2 mL). The reaction mixture was stirred for 1 hour at room temperature. The reaction was quenched with a saturated solution of Na2CO3 (300 mL) and the aqueous phase was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated to yield N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide (33.8 mmol, 9.30 g, 98%) as a beige solid.

Aufarbeitung

  1. customAfter evaporation
  2. dissolutionthe crude product was dissolved in DCM (30 mL)
  3. customThe reaction was quenched with a saturated solution of Na2CO3 (300 mL)
  4. extractionthe aqueous phase was extracted with DCM
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationwas filtered
  7. concentrationwas concentrated

Quellen und Nachweise

ORD-Eintrag
ord-1a49b91c957744b1b47ec64285602453
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524718B2

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